(5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine

Base Information

• Chemical Name: (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine
• CAS No.: 749924-30-9
• Molecular Formula: C₄₈H₅₈O₃SeSi₂
• Molecular Weight: 818.118
• Mol file: 749924-30-9.mol

Synonyms:(5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine

Chemical Property of (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine

There total 2 articles about (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

Phenylselenyl chloride (5707-04-0) + (8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-methylene-2,3,4,7,8,9-hexahydrooxonine (749924-29-6) → (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine (749924-30-9)

Guidance literature:

Phenylselenyl chloride; (8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-methylene-2,3,4,7,8,9-hexahydrooxonine; In tetrahydrofuran;

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1055/s-2004-825627

Reference yield:

(Z)-(8S,9R)-8-tert-butyldiphenylsilyloxy-9-tert-butyldiphenylsilyloxymethyl-2,3,4,7,8,9-hexahydro-oxonin-2-one (148903-89-3) → (5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine (749924-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 83 percent / toluene / 0.5 h / 110 °C

2.1: tetrahydrofuran

2.2: 52 percent / LiAlH₄ / tetrahydrofuran / -78 °C

In tetrahydrofuran; toluene; 1.1: Petasis methylenation;

DOI:10.1055/s-2004-825627

Reference yield: 81.0%

(5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine (749924-30-9) → (2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde (749924-31-0)

Guidance literature:

(5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-(phenylselenylmethyl)-2,3,4,7,8,9-hexahydrooxonine; With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at -78 ℃; for 0.416667h; Inert atmosphere;

With sodium acetate; acetic anhydride; In tetrahydrofuran; at -78 ℃; for 1.91667h; Reflux; Inert atmosphere;

With potassium carbonate; In methanol; dichloromethane; for 16h; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.03.010

upstream raw materials:

Phenylselenyl chloride

(8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2-methylene-2,3,4,7,8,9-hexahydrooxonine

(Z)-(8S,9R)-8-tert-butyldiphenylsilyloxy-9-tert-butyldiphenylsilyloxymethyl-2,3,4,7,8,9-hexahydro-oxonin-2-one

Downstream raw materials:

(Z)-(2S,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonine-2-carbaldehyde

[(Z)-(2R,3S,9R)-3-(tert-Butyl-diphenyl-silanyloxy)-9-((E)-2-methyl-buta-1,3-dienyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-methanol

(2R,5Z,8S,9R)-8-(tert-butyldiphenylsilanyloxy)-9-(tert-butyldiphenylsilanyloxymethyl)-2,3,4,7,8,9-hexahydrooxonine-2-carbaldehyde

(E)-3-[(Z)-(2R,8S,9R)-8-(tert-Butyl-diphenyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,3,4,7,8,9-hexahydro-oxonin-2-yl]-2-methyl-propenal

Refernces